EXCERPT

The Night Sinatra Happened

THE VOICE OF AMERICAPerforming in New York, April 1943. At this stage of his career, Sinatra was caricatured as “Swoonatra.”

As 1940 approached, a skinny, big-eared Italian-American kid with a hotly seductive voice was aiming to topple Bing Crosby’s cool supremacy and turn American popular music on its head. But first Frank Sinatra needed the big-band boot camp of a man whose style and talent he idolized: the trombone-playing Tommy Dorsey. In an excerpt from his new Sinatra biography, the author describes how the rising young star suddenly turned the tables on Dorsey, eclipsing the equally ambitious bandleader, then shooting solo into the stratosphere.

The voice was still developing in the spring of 1939—it would continue to develop for the next 50 years. It wasn’t as rich as it would be even five years later. But its DNA was there, the indefinable something composed of loneliness and need and infinite ambition and storytelling intelligence and intense musicality and Hoboken itself, the thing that made him entirely different from every other singer who had ever opened his mouth.

And Frank Sinatra had one more astounding thing at 23: a plan. He was going to knock over Bing Crosby. He knew it in the pit of his gut. But not even his new wife, Nancy, knew the true height of his hubris.

Frank had struggled and scrambled, at first, to gain even rudimentary success as a professional singer. He’d chased after Hoboken bands that didn’t particularly want him but saw uses for the Chrysler convertible and the musical arrangements his mother, Dolly, had bought him with her earnings as a midwife and abortionist. He’d sung for pennies in Irish and Italian social clubs and American Legion halls (and sometimes had pennies thrown into the megaphone he used for amplification). He’d sung for carfare, or less, on the radio. He’d foisted himself (with Dolly’s aid) on a vocal trio called the Three Flashes and, after the group surprised everyone by taking first place on Major Bowes’ Amateur Hour, set about overshadowing his partners.

With Dolly’s intercession once more (she had serious political juice in northern New Jersey), Frank had wangled his way into a singing-waiter job at a nightclub on the Palisades called the Rustic Cabin. Why? The Cabin had a telephone-wire hookup to the New York radio station WNEW, a station the kind of people Sinatra wanted to be heard by listened to—people such as the band singer Louise Tobin and her husband, the trumpeter and bandleader Harry James. It was Tobin who happened to catch Frank singing on WNEW one night in the spring of 1939 and thought enough of him that she woke up her husband and said, “Honey, you might want to hear this kid on the radio.” And it was James who decided soon thereafter, at the end of a long day of performing and traveling, to take a side trip to the Rustic Cabin.

He liked what he heard. “This very thin guy with swept-back greasy hair had been waiting tables,” James recalled many years later. “Suddenly he took off his apron and climbed onto the stage. He’d sung only eight bars of ‘Night and Day’ when I felt the hairs on the back of my neck rising. I knew he was destined to be a great vocalist.”

James offered him a contract on the spot: $75 a week. It was quite an offer, three times what Sinatra was currently making. What James neglected to say was that there were some weeks (he wasn’t especially good with money) when he didn’t have $75 to his name.

Since Harry had created Connie Haines that morning (that was the name he had conjured on the spot for his new girl singer, née Yvonne Marie Antoinette JaMais), he was feeling lucky. “Sinatra” was too Eye-talian, he said. How about Frankie Satin? It went nice with that nice smooth voice of his.

Just a moment before, Sinatra recalled in later years, he had been grasping James by the arm, incredulous at the offer, making sure his main chance didn’t get away. Now, as Connie Haines remembered sharply 67 years after that night, the singer’s eyes went cold. “Frank told Harry, ‘You want the singer, take the name,’ ” Haines said. “And walked away.”

Sinatra had already tried an Anglicized stage name—Frankie Trent—very briefly, a couple of years before. And while “Frankie Trent” was bad enough, “Frankie Satin” was much, much worse—it made “Connie Haines” look like sheer genius. It wasn’t even Anglicized; it was 100 percent corn oil. As Sinatra told the writer Pete Hamill, “Can you imagine? Is that a name or is that a name? Now playing in the lounge, ladies and gennulmen, the one an’ only Frankie Satin.…If I’d’ve done that, I’d be working cruise ships today.”

But when Frank walked away, James came right after him. The defiantly un-renamed Frank Sinatra joined Harry James and His Orchestra on June 30 as they opened a week-long engagement at the Hippodrome, in Baltimore. He was so new that he wasn’t even listed on the bill. Still, some girls in the audience quickly got the idea: “After the first show, the screaming started in the theater, and those girls came backstage,” Connie Haines told Peter J. Levinson, for his Harry James biography, Trumpet Blues. “There were about twenty of them… It happened, it was real, it was not a gimmick.”

Not a gimmick at all. The Voice—might as well start capitalizing it here—was simply working its spooky subliminal magic. Did it help that the singer was clearly in need of a good meal, that his mouth was voluptuously beautiful, that his electric-blue eyes were attractively wide with fear and excitement, that he knowingly threw a little catch, a vulnerable vocal stutter, into his voice on the slow ballads? It helped. It whipped into a frenzy the visceral excitement that his sound had started. But the sound came first. There was simply nothing like it.

“A Little Too Much Pash”

The singer was a genius, the trumpeter-leader a kind of genius. The band was terrific. The world would fall at both men’s feet in a few years. But not everyone was thrilled at first: both Sinatra and Harry James seemed to be simply ahead of their time. James blew hot and hard, a style that delighted critics but didn’t always sit well with country-club and society-ballroom and nightclub audiences. They didn’t want to listen, they wanted to dance close and slow … and go home and make babies who would grow up and go to country clubs and society ballrooms and dance close and slow. A nice society band, a Lawrence Welk or an Eddy Duchin outfit, was simply more adequate to the purpose than a group that made you sit up and take notice.

And Frank Sinatra—well, Sinatra, for his part, was an acquired taste at first. Especially for the critics. During a Chicago stand, a Billboard reviewer wrote that Sinatra sang “the torchy ballads in a pleasing way in good voice,” but then went on: “He touches the songs with a little too much pash, which is not all convincing.”

Or maybe all that pash was simply unsettling because it was so new. Among the smooth-as-silk baritones of the day, led by Bing Crosby, Sinatra was an anomaly, a hot artist rather than a cool one, a harbinger of his own singular future.

Harry James, too, was a hot artist: a hepcat, a weed-puffing wild man. He was also a strangely self-defeating character—alcoholic, remote, and persistently broke. That summer, he lost everything he had in a settlement over an auto accident. (Connie Haines, whose salary he could no longer afford, had to leave.) And in a country crowded with big-band talent—Tommy Dorsey, Benny Goodman, Charlie Barnet, Count Basie, Jimmy Dorsey, Duke Ellington, Bob Crosby, Jimmie Lunceford, Glenn Miller, and Artie Shaw were all crisscrossing the land with their outfits in the swinging late 30s and early 40s—James was having a hard time making a go of it. Some nights, as the band worked their way westward, they pulled down only $350—and that had to pay 17 musicians and a bus driver, not to mention defray the costs of food, gas, and accommodations. There were times the outfit seemed snakebit. Bookings were scattershot; morale was sinking fast. Then, in September 1939, while the band played the Hotel Sherman, in Chicago, James finally got some good news: MCA, the band’s booking agency, had landed them a big gig at a big venue, the famed Palomar Ballroom, in Los Angeles, where Benny Goodman and his band had started the swing era overnight with a fabled performance in August 1935. There were smiles on the bandstand at last.

On October 2, 1939, the Palomar burned to the ground.

MCA snagged James’s band an alternative engagement, at a Beverly Hills dining-and-dancing establishment called Victor Hugo’s, run by a character named Hugo Aleidas. Unfortunately, the restaurant turned out to be a small, stuffy room, with canaries in gilt cages for decoration: the kind of place where dulcet society bands such as Guy Lombardo’s fit in just fine. Not only did Harry’s band play hot and sweet, it played loud. At first the management tried erecting a canopy over the bandstand to muffle the sound. When that proved insufficient, the horn players were asked to stuff handkerchiefs into the bells of their instruments. By the end of the week, customers were voting with their feet—James, Sinatra, and company were playing to half-full houses. Finally, even Sinatra’s ballads were to no avail: One night, while he was in the middle of “All or Nothing at All,” no less—he would have a huge hit with it a few years later—Aleidas ran out onto the dance floor, waving his arms and shouting, “Stop! No more! Enough!” To add insult to injury, and to underline Harry James’s perfectly bad business luck, the owner refused to pay the band.

Sinatra felt a growing desperation. He had the goods and he knew it. He had learned a lot from Harry James—he loved Harry James. But he knew he needed to get out. He dreamed of singing with Benny Goodman or Count Basie, the way Billie Holiday had, or even Tommy Dorsey, who ran the Rolls-Royce of bands and really knew how to feature singers.

In the meantime, James and his band were limping home to New York. MCA had managed to get them a week at a Los Angeles movie theater and another week at the Golden Gate Theatre, in San Francisco, but then came the interminable drive over the Rockies and the Great Plains, the one-nighters in Denver and Des Moines and Dubuque. They lived on hot dogs and Cokes and candy bars, flirted halfheartedly with the local girls as they headed toward their next stand: a week at the Chicago Theatre, and a Christmas benefit thrown by the mayor of the Windy City, boss Edward J. Kelly. Riding, riding through the night. As the rest of the band played cards and laughed or told dirty jokes or slept and snored, Sinatra sat by himself in the back of the bus, his jacket folded over his eyes, with one thought in mind, over the Rockies, across the Great Plains, across the unendingly huge country that did not yet lie at his feet but would: On the bill at the Chicago Theatre would be Tommy Dorsey.

He was one tough son of a bitch, the second son of a horn-playing family from the coal-mining hills of eastern Pennsylvania, one of the starkest places on earth. He was just 35, but 35 was more like 45 in those days, and coming from where he’d come from, and having done what he’d done, Tommy Dorsey had a hundred thousand miles on him. He was five ten and ramrod-straight, with a square, pitiless face, a hawk nose, cold eyes behind little round glasses. He looked just like a high-school music teacher—he knew it, others knew it, and he tried to shift the impression by dressing more elegantly than other bandleaders (he had an immense wardrobe, more than 60 suits and sport jackets) and standing taller (he wore lifts in his shoes and tended to pose for the camera with his trombone slide extended alongside him, to emphasize the vertical line). His ambition was titanic, his discipline incomparable. He could (and often did) drink himself into a stupor after a gig, sleep three hours, then get up at six A.M., play golf, and be as fresh as a daisy for the day’s work. No matter how long the road trip or how taxing the engagement, he was never seen in rumpled clothes. He did precisely what he wanted, when he wanted, took shit from nobody, and played an absolutely gorgeous trombone. “He could do something with a trombone that no one had ever done before,” said Artie Shaw, who was stingy with compliments. “He made it into a singing instrument…Before that it was a blatting instrument.”

Dorsey had a massive rib cage and extraordinary lung power. He could play an unbelievable 32-bar legato. What he couldn’t do, precisely, was improvise. He hopelessly idolized the legendary Texas trombonist and vocalist Jack Teagarden, a great jazz artist, a man who could transform a song into something new and sublime and dangerous. Dorsey didn’t transform; he ornamented, he amplified. But when he blew those glorious solos, measure after silken measure seemingly without a pause for breath, you forgot about jazz: Tommy Dorsey made his own rules. His theme song, “I’m Getting Sentimental over You,” spoke for itself—and gave him a deliciously corny nickname, the Sentimental Gentleman of Swing.

For three years he entranced the fox-trotting masses with his long, sweet solos. But swing grew hotter as the 1940s approached—even Glenn Miller’s band was starting to sound punchier—and the critics began to carp about Dorsey’s monotonous mellowness. The truth is, Tommy Dorsey was starting to get bored with himself. Any sentimentality that he possessed was buried under layers of toughness and anger. And—except when the microphone was on—he wasn’t particularly gentlemanly. Before his public grew bored, too, the ever restless, insatiably ambitious bandleader decided to make some changes.

That summer, he hired away Jimmie Lunceford’s genius arranger, Melvin James “Sy” Oliver. Oliver attracted jazz musicians to Dorsey’s band, musicians such as the ace trumpeter Zeke Zarchy and the percussively and temperamentally explosive 22-year-old drummer Buddy Rich, who had become a national phenomenon that year while playing for Artie Shaw.

Soon afterward, though, Dorsey lost his singer of nearly four years, Jack Leonard. Leonard had been with the band since he was about 19, crisscrossed the country many times in the ice-cold or baking-hot band bus, dutifully laid down the workman-like vocals on more than 40 hit Dorsey recordings, and had felt the Old Man’s occasional warmth but—more often—suffered his tongue-lashings. One evening the young vocalist simply walked off the bandstand and never came back. Dorsey needed a new singer, and fast.

In Chicago one night, the bandleader was having dinner with a pal named Jimmy Hilliard, the music supervisor for CBS, and bemoaning his boy-singer problem. “Have you heard the skinny kid who’s singing with Harry James?” Hilliard asked. “He’s nothing to look at, but he’s got a sound! Harry can’t be paying him much, maybe you can take him away.”

Dorsey had quickly filled the breach caused by Leonard’s departure with a baritone named Allan DeWitt. But DeWitt was merely adequate, and Tommy Dorsey wasn’t interested in adequacy.

Then he heard Sinatra for himself.

The band was filing through the lobby of the Palmer House when the music coming from a radio stopped Dorsey in his tracks. The song was “All or Nothing at All.” He beckoned to his clarinetist, Johnny Mince. “Come here, Johnny. I want you to hear something,” Dorsey said. “What do you think?”

The next night he sent his manager, Bobby Burns, to Mayor Kelly’s Christmas party to hear James’s band. After the performance, Burns slipped Harry’s boy singer a note scribbled on a strip torn from a sandwich bag. Frank Sinatra’s heart thumped hard when he saw the pencil scrawl on the grease-spotted brown paper: the note indicated Dorsey’s suite number at the Palmer House and the time Frank should show up.

Sinatra saved that scrap of paper for a long time.

It was a careful dance, the kind of minuet men do when approaching each other on a matter of importance. Sinatra had been aware, with each mile Harry James’s rickety band bus traveled eastward, of Dorsey’s looming presence in Chicago: it was like entering the gravitational field of an enormous dark star. And Dorsey, always calculating, had registered something when Jimmy Hilliard mentioned Sinatra. That something clicked into place when Dorsey heard the song on the radio: he had already met this kid once.

A few years earlier Sinatra had been auditioning for a young bandleader when Dorsey walked in. Tommy fucking Dorsey. Sinatra got so flustered at the sight of that cold Irish puss (Dorsey looked like a goddamned emperor or something) that he forgot the lyrics of the song he was singing and froze—literally opened his mouth and nothing came out.

Sinatra, of course, remembered the occasion intimately as one of his great gaffes, like spilling a drink on a pretty girl’s dress or calling someone important by the wrong name. He still blushed just thinking about it. This meeting in Chicago would be his one and only chance to set things right, his one and only chance with the great man, and it must—it must—go right. There would be no third chance. He barely slept that night, thinking of Tommy Dorsey’s tough face and his perfect suits and, most of all, his gorgeous sound, those long, beautiful melody lines that backed a singer the way the purple velvet in a jewel box backed a diamond bracelet.

At two P.M. on the dot, Dorsey greeted Frank at the door of his suite wearing a silk dressing gown over suit pants, shirt, and tie. He exuded a manly whiff of Courtley cologne. His square gold cuff links were engraved TD.

Sinatra felt weak in the knees.

A strong handshake and that icy stare, from slightly above, with the very faintest of smiles. “Yes, I remember that day when you couldn’t get out the words.”

And damned if it didn’t almost happen again: Frank’s mouth fell open and, for a second, nothing came out. He had to clear his throat to get his heart started again, and with that sound, miraculously, a sentence emerged.

Well, he’d been pretty nervous that day. He was pretty nervous today too.

The smile warmed just a degree or two. Dorsey told Frank to call him Tommy. He told him he’d like to hear him sing. Did Frank think he could manage that? He had a few of the boys waiting up in the ballroom, Dorsey said. Did Frank know “Marie”?

Frank had only heard Jack Leonard sing it about a million times with that band behind him, had only imagined himself in Leonard’s place about a million times. And Sinatra knew he could leave Jack Leonard in the dust. If he could get the words out.

And that was what Tommy Dorsey heard that afternoon in the Palmer House ballroom as Sinatra stood by the piano, not nervous at all now, but as excited to be following Dorsey’s dazzling trombone lead-in as he had ever been excited by a wide-spread pair of silky thighs …

Dorsey nodded, almost smiling, as Sinatra sang; seeing his reaction, Sinatra smiled and sang even better.

When Frank was done, Tommy told him he wanted him to come sing with the band. If Harry would let him go. Dorsey couldn’t pay him a lot to begin with—only $75 a week—but they could talk later on.

Sinatra didn’t even hear the figure.

Did Christ Pay the Disciples?

He joined the Dorsey band on the road a month later. Accompanying him were his old pal Hank Sanicola, to play rehearsal piano and swat off pests, and a Hoboken kid named Nick Sevano, to lay out Frank’s clothes and run for coffee. How the singer could afford not one but two hangers-on at $75 a week is an almost theological question, answered nowhere in the vast body of Sinatriana—did Christ pay the disciples? And as to whether Sinatra met up with his new boss in (as has variously been reported) Minneapolis or Sheboygan or Milwaukee or Rockford, Illinois, there is no consensus. This much is universally agreed upon, however: he knocked the socks off all who were fortunate enough to be present.

“The first time I heard him, we were onstage in Milwaukee, and I had not even met him,” Jo Stafford recalled. “Tommy introduced him and he came out and sang ‘South of the Border.’ ”

Her interviewer was perplexed. Many accounts said the number was “Stardust.”

Stafford, though a very old lady now, shook her head vigorously. “ ‘South of the Border,’ ” she insisted.

Almost 70 years earlier, at 22, she had helped form Tommy Dorsey’s reconstituted sound when he hired her singing quartet, the Pied Pipers. The group joined the band in December 1939, while Sinatra fulfilled his obligation to Harry James. And the Pipers were sitting on the stage in Milwaukee or Sheboygan or Minneapolis or Rockford when Sinatra appeared, to Stafford’s mind, straight out of the blue.

Had she even heard him on the radio at that point?

“Never even heard of him,” she said. “But I sure knew this was something. Everybody up until then was sounding like Crosby, but this was a whole new sound.”

Was it ever. In fact, Bing’s days were numbered.

Not commercially. Buoyed by his movie career, his matchless radio presence, and his ever rising record sales, Crosby’s stock was headed nowhere but up, and would continue to flourish for more than 20 years. But a new ballad singer had taken the field, and though America didn’t know it yet, the country’s heart hung in the balance. Bing had specifically instructed his lyricist, the great Johnny Burke, never to put the words “I love you” into one of his numbers: it simply wasn’t a sentiment the star could carry off head-on. His humor—America loved him for his dry humor—would have been undercut by it. His wooing was more oblique. There was nothing oblique about Frank Sinatra. While Bing’s power was his cool warmth, Frank’s was his unabashed heat.

“Frank really loved music, and I think he loved singing,” Jo Stafford said. “But Crosby, it was more like he did it for a living. He liked music well enough. But he was a much colder person than Frank. Frank was a warm Italian boy. Crosby was not a warm Irishman.”

So, suddenly, in the land of Crosby sound-alikes, in the year of our Lord 1940, when Americans heard their president speak on the radio in god-like aristocratic tones, when they heard American movie actors declaiming in indeterminate English-y accents, here was something new: a warm Italian boy. A boy with a superb voice that was also a potent means of communicating all kinds of things that white popular singers had never come close to: call it romantic yearning with hints of lust behind it, or call it arrogance with a quaver of vulnerability. In any case, it was a formula absolutely irresistible to blindsided females—not to mention impressed males, who very quickly began using Sinatra as background to their wooing. As Daniel Okrent wrote in a 1987 Esquire article, “Sinatra knew this: the male of the species has never developed a more effective seduction line than the display of frailty.”

Jo Stafford was sold; most in the band weren’t. At first the veterans, who had all been fond of the sweet-tempered Jack Leonard, simply froze the newcomer out. And then there was Buddy Rich. On Sinatra’s first one-nighter, he noticed that the bus seat next to the drummer was empty—not much of a surprise, given Rich’s abrasive personality. (When Dorsey introduced Sinatra to Rich, it was with these words: “I want you to meet another pain in the ass.”) So Sinatra sat down. The two young men—Frank was 24, Buddy 22—got to talking, and, lo and behold, they hit it off. After a few days on the road, Rich told Sinatra, “I like the way you sing.” It was extravagant praise, coming from one of the biggest egomaniacs in the business—little did Sinatra realize how heartfelt the comment was. (In later life, Rich admitted he had had to turn his face to hide his tears when Sinatra sang “Stardust.”) The two became roommates. It sounds like a sweet story. It was doomed from the start.

Sinatra’s days as an only child set the pattern: he had never been much for sharing a room—or much of anything else, for that matter. (Traveling with the James band over most of the first year of his marriage, he had barely lived with his young wife, the former Nancy Barbato.) The end to the Sinatra-Rich honeymoon came when Sinatra insisted on clipping his toenails in their hotel room at two A.M. Remarkably, Rich told his biographer Mel Tormé that the insomniac singer had also kept him awake by reading till all hours. Among the many big-band personnel traveling the United States in the late 1940s, Sinatra and Artie Shaw may have been the only two men keeping late hours with, now and then anyway, a book.

But the real reason the singer and the drummer split was that each felt he was Dorsey’s true star. (Tommy Dorsey knew he and he alone was the star, another problem altogether.)

Of course, Dorsey’s name was printed in the biggest type on the band’s posters, but the leader decided whose name would be featured under his, an honor with purely commercial underpinnings that depended on—and, in a circular way, determined—which band member was hottest. Often it was trumpeter Bunny Berigan; lately, in early 1940, it had been the new star, Rich. But soon enough it would be Sinatra all the way.

In the beginning, Sinatra set out to learn everything he could from Dorsey, personally and musically. What thrilled him at the outset was simply the way Dorsey carried himself, the way he handled his fame and power: his erect posture, his smooth patter on the bandstand and at radio microphones, his perfect wardrobe (he was even photographed, during a summertime stand in New York, wearing tailored Bermuda shorts with his jacket and tie). Not to mention his eye for the ladies and his heavy after-hours drinking. Sinatra, always an obsessive, copied even some of the tiniest details—Dorsey’s Courtley cologne, his Dentist Prescribed toothpaste.

But the most important lessons the singer learned from the leader were musical. Much has been made of the magical breath control Sinatra supposedly learned at Dorsey’s feet—or, rather, at his back, while he was playing his trombone: “I used to watch Tommy’s back, his jacket, to see when he would breathe,” Sinatra said. “I’d swear the sonofabitch was not breathing. I couldn’t even see his jacket move… I thought, he’s gotta be breathing some place—through the ears?”

Dorsey did indeed have spectacular breath control, through a combination of anatomical good fortune and artful deception. His trick was to take an extra breath, when he needed one, through a pinhole which he would form at the corner of his mouth and which he would shield from prying eyes with his left hand, which, in standard trombonist’s form, was held close to the instrument’s mouthpiece. Hence those 32-bar (or 16-bar, depending on who’s telling the story) legatos.

But his long trombone lines were more than trickery or showmanship: they were the melodic essence of his art. His band’s numbers usually began with a solo by the lead trombonist, to (1) instantly announce the presence of T.D. and (2) quickly tell the story of the song. Both things were crucial on the radio, which, as the main medium for mass communication of the day, had a tremendous imaginative force that all began with sound. And Dorsey’s whole band—which, after all, was his true instrument, a 16-piece extension of his towering personality—needed to be up to the task. “Tommy sometimes used to make the whole orchestra (not just the trombones) play from the top of a page clear down to the bottom without taking a breath,” saxophonist Arthur “Skeets” Herfurt told Sinatra biographer Will Friedwald. “It was way too many bars! But I sure developed lung power… Everybody in the band would learn to play like Tommy did.”

Clever as he was, Sinatra instantly realized he would have to raise his game vocally. Though, as his first recordings with the band show, he began rather pallidly, trying to fit in and generally hold his own, he was watching and learning every second. Tommy Dorsey was a superstar (even if that vulgar word hadn’t yet entered the vernacular), and Sinatra was, by God, going to be one, too. Even bigger. But copying Dorsey’s breath control was a far more powerful statement than copying the cologne or toothpaste he used. Sinatra had heard other singers, even very good ones, take a breath in the middle of a phrase, and he thought it sounded lousy. It showed artifice, just like the hoked-up accents and stuffy styles of most vocalists in those days. It said, This is a singer, singing a song. Most of those guys—even the very good ones—never sounded as if they felt what they were singing, as if they really believed it. Singing the phrase straight through showed he truly understood the words.

A message that was not lost on his listeners. He saw the way the girls stared at him as he sang. He was telling them something, a story of love, and they were listening. (He could continue the story whenever he wanted, on or off the stage.) They didn’t stare at Bing that way.

“His Whole Person Seems to Explode”

No one ever told the Sinatra story better than Sinatra himself. And one of the great chapters was the account of how he had developed powers of breath control even more extraordinary than those of the short-lived Dorsey (who—with horrible irony—died of asphyxiation, choking to death on his own vomit in his sleep after a heavy meal at age 51, in 1956). After Dorsey mentioned offhandedly that he’d built up his lung capacity by swimming underwater, Sinatra decided that he too would swim laps underwater, at the Stevens Institute’s indoor pool in Hoboken—and let the world know about it. Not only that: he would also run laps on the Stevens track. It has the feeling of a Hollywood montage. You can practically see the big varsity S on Sinatra’s sweatshirt as he pounds the cinders of that Stevens quarter-mile.

And yet, while Sinatra doubtless did some underwater swimming and ran some laps, it’s hard to imagine an inveterate night owl and hedonist, fully engaged in the grueling existence of a touring swing band, taking on any sort of concentrated training regimen.

Jo Stafford insisted that all the mythic accounts of underwater swimming were just that: mythological. The true story, she said, was anatomical. “You can have a big enough rib cage to take a deep breath,” she said. “And also know how to let it out. You can sing a note and use half as much breath as most people do. I think that if you want to learn to do that, you can. Frank certainly could. I could. Tommy also.”

Maybe Frank did have an extra-large rib cage; maybe, once the band came east from Chicago in February of 1940 (to start a New York stand that would continue through the summer), he simply shifted into a new gear, swimming and running. At any rate, he was gathering a huge new power, a kind of sexual supercharge. Sammy Cahn recalled watching Sinatra sing with Dorsey: “Frank can hold a tremendous phrase until it takes him into a sort of paroxysm—he gasps, his whole person seems to explode, to release itself.”

Zeke Zarchy could see it from the trumpet section: “The audience wouldn’t let him off the stage,” he recalled. “This scrawny kid had such appeal. I had never seen a vocalist with a band go over like that.”

The band’s first date after it returned from Chicago was at one of the biggest clubs in the East, Frank Dailey’s Meadowbrook, on Route 23 in Cedar Grove, New Jersey. “It was at the Meadowbrook,” Peter Levinson writes in his biography Tommy Dorsey: Livin’ in a Great Big Way, “that Dorsey first gave Sinatra, rather than to Buddy Rich, featured billing. Buddy immediately expressed his anger to Tommy, but to no avail. In retaliation, he speeded up the tempo on slow ballads behind Sinatra or played loudly behind him.”

Things would escalate from there. But Rich was fighting a losing battle—and he knew it, which riled him up even more. He felt gypped: he had signed on with Dorsey to propel jazz, and now the ballads (totally boring to keep time to), and the ballad singer, were taking over. And no matter how blazing a drummer’s solos, he sits at the back of the band; the singer stands in front. Literally and figuratively, Frank Sinatra was beginning to stand in front of everyone else.

Everyone.

Tommy Dorsey would have laughed in the face of anyone who told him that his boy singer, this pain-in-the-ass little guinea, was bringing the primacy of the big band to an end and single-handedly ushering in the age of the solo vocalist. The Dorsey empire was running smoothly, its ruler a superb businessman as well as a great bandleader. His band hit the ground running when it reached the Big Apple.

For most of March, Sinatra headlined at the Paramount, the crème de la crème of big-band venues. The girls were so gaga for him that they would line up in the dark hours ahead of time for the first show—it was at nine A.M.—and then, when that show was over, they would refuse to leave, staying for five more. Frank emulated a brilliant publicity stunt of Dorsey’s, bringing out a big tray of food after the first show, to tide over his increasingly fanatical public. At the end of the day, he had to be escorted by the police to the Hotel Astor, just a half-block up Broadway.

Meanwhile, a little blast from the recent past arrived in the form of Connie Haines, whom, unlike Harry James, Tommy Dorsey could very much afford. And unlike the Pied Pipers, who—gorgeously as they sang—were strictly background, Haines was a star, a pint-size 19-year-old with big eyes, a perky figure, a thick Savannah, Georgia, accent, and a big voice. She could really sing, and swing, and audiences ate her up (and Dorsey, a great showman, knew it). And Sinatra hated her thunder-stealing guts. He was the show. “Go ahead, do your thing, cornball,” he would snarl at her as she jitterbugged, grinning, around the big stage.

But he would soon have the spotlight all to himself. Beginning in May, the band was booked to play the Astor’s gloriously posh Roof Garden—it had a thousand-foot tree-lined promenade, with lights twinkling like stars among the branches. For New York’s glitterati, the Dorsey stand was a much-anticipated event. Sinatra too was all aflutter. The Astor was Class with a capital C, and the singer, who from an early age craved class just about as much as he craved sex (but found it much less attainable), was more nervous than he had ever been about a show. It was one thing to play the Paramount, with its great sea of undifferentiated faces; it was quite something else to entertain the rich at close hand. He could depend on a certain number of swooning teenage girls (it was prom season), but the audience at the Astor would consist mainly of adults—wealthy, arrogant, jaded adults. With an exquisitely calibrated social sense born of deeply held feelings of inferiority—Italians had risen in the American public’s estimation since Marconi and Toscanini, but not much—Sinatra felt an entirely reasonable fear of what he was up against.

Still, fear got him excited. And on opening night, Tuesday, May 21, 1940, he got the Astor excited. Sinatra’s first number teamed him with the Pied Pipers, and—as was distinctly not the case when he shared the stage with Haines—his respect for his fellow performers led him to vocalize selflessly and beautifully. It was yet another string to Sinatra’s bow: “When you sing with a group, it takes a certain amount of discipline, and Frank was excellent at it,” Jo Stafford said. “You can’t wander off into your own phrasing. You’ve all got to do exactly the same thing at exactly the same time. Very few solo singers can do that. He could. When he sang with us, he was a Piper, and he liked it and did it well. I don’t know any other solo singer, solo male singer especially, that can do that.”

That was the point: he wasn’t like other singers. And on the next number, the hypnotically beautiful “Begin the Beguine,” the stage and the song were all his. And, as 23-year-old pianist Joe Bushkin, who’d just joined the band in April, recalled, “He wound it up with a nice big finish, and the place went bananas!” The formerly jaded crowd, which had stopped dancing to listen, was screaming for an encore—but “Begin the Beguine” was the only solo feature Sinatra did with Dorsey at the time.

Canny showman that he was, Dorsey put his own ego on hold and stopped the band. If they wanted an encore, they’d get one. “Just call out the tunes,” he told Sinatra, “and Joey will play ’em for you.”

This went fine for three or four numbers, Bushkin said, until Sinatra turned around and said, “Smoke Gets in Your Eyes.” The lovely Kern-Harbach tune has a notoriously tricky middle section, a chord modulation that looks great on paper but can be hell to pull from memory. Under pressure, Bushkin simply blanked. “Next thing I know,” he said, “Frank was out there singing it all by himself, a cappella. I was so embarrassed. I mean, Jesus, all the guys were looking at me, so I just turned around and walked away from the piano!”

The cream of New York society—swells in dinner jackets; dames in gowns; a few hundred fancy prom kids, all dressed to the nines—stood hushed, craning their necks to see, while the skinny boy with the greasy hair filled the big room with song, all by himself.

“That,” Joe Bushkin said, “is the night that Frank Sinatra happened.”

Just two days later, Dorsey, and a stripped-down core unit that he called the Sentimentalists, went into the RCA recording studio in Rockefeller Center and took another stab at a number they had tried, without much success, a month earlier. The song, a mournful ballad written by a pianist named Ruth Lowe in memory of her late husband, was called “I’ll Never Smile Again.” The May 23 version moves at a dreamy-slow tempo. It begins with a piano intro, followed by the perfect five-part harmony of the four Pied Pipers plus Sinatra, singing the first stanza and a half:

I’ll never smile again
Until I smile at you
I’ll never laugh again

Then Sinatra comes in alone: “What good would it do?” he sings, aspirating the initial “wh” of “what” with such plummy precision that it comes out “hwat”—a pronunciation that would not have sounded amiss to Cole Porter’s society crowd.

It sounded just great to America. When the record was released, five weeks later, it claimed the No. 1 spot on the Billboard chart and stayed there for 12 weeks, turning Frank Sinatra into a national star. Meanwhile, on the strength of Frank’s éclat, the Dorsey band’s initial booking of 3 weeks at the Astor was extended to 14.

Did Tommy Dorsey come up with more solo ballads for Sinatra to sing? You bet he did. Just like that, the cart was pulling the horse.

And Sinatra kept thinking about what Tommy had said when he sent him home one night after Frank and Buddy Rich had gotten into a fistfight: I can live without a singer tonight, but I need a drummer. Ultimately, no matter how popular he got, he was dispensable. But then, that could work the other way, too.

“I kept thinking to myself, ‘I’ve got to climb a little higher in this next year,’ ” Sinatra told journalist Sidney Zion, at a Yale lecture, 45 years later. “I gave myself calendar times. What could I do in six months? How far could I go?”

Bullets Durgom was finding out how far. Durgom, Dorsey’s short, roly-poly record-promotion man (his real first name was George; he had acquired the Runyonesque handle by moving fast), had the job of visiting radio stations, drumming up interest in the band’s new sides. But what radio stations in 1941 were less and less interested in were Tommy Dorsey instrumentals. “All they wanted to hear about,” Durgom later told critic George T. Simon, “was Frank.”

“This boy’s going to be big,” Durgom said at the time, “if Tommy doesn’t kill him first. Tommy doesn’t like Frank stealing the show—and he doesn’t like people who are temperamental like himself.”

In May, Billboard named Sinatra top band singer of the year.

He was the one they came to see. Gradually at first and then suddenly, a great national tide of girls surged up, their freshly sprouted breasts swelling with passion for him. Only a minute earlier, they’d been flat-chested kids, playing with their dollies in the dry dust of the Depression. Now they wore calf-length skirts and ankle-length white socks—bobby socks—with saddle shoes or Mary Janes, and they had a little bit of money in their purses: the Depression was over. Some newspaperman called them bobby-soxers, and it stuck.

When he sang the long, long lines of those slow ballads, sounding as though his heart might burst any second, why, those girls felt as though their hearts might burst, and they just had to cry out, Frankiee!

Dorsey stood, straight-backed and incredulous, the first time it happened. They were screaming, pretending to faint, really fainting, for Christ’s sake, like Holy Rollers at a revival meeting. Tommy smiled indulgently (they were ticket buyers, after all), but actually felt a kind of genteel horror: What in the goddamned hell was the world coming to?

“I used to stand there on the bandstand so amazed I’d almost forget to take my solos,” the bandleader remembered years later. “You could almost feel the excitement coming up out of the crowds when that kid stood up to sing. Remember, he was no matinee idol. He was a skinny kid with big ears. And yet what he did to women was something awful.”

Tommy smiled about it all—at first. At first, he even made fun of Sinatra. When the girls would start swooning, he would stop the band and have the musicians swoon right back at them. “This inspired the girls to go one better,” Dorsey recalled, “and the madness kept growing until pretty soon it reached fantastic proportions.”

In late August 1941, the band started another run at the Paramount in New York, a three-week engagement that had sold out—unlike the previous year’s stand—strictly on the basis of Sinatra. The theater’s most spectacular feature was its gigantic moving stage that rose right up out of the orchestra pit when the show began and sank back down when it was over. One night, after the band closed with “I’ll Never Smile Again,” and the stage began to descend, a couple of bobby-soxers leaned over and grabbed the singer’s bow tie, one on each end, and wouldn’t let go. “He was hanging there,” Connie Haines remembered. “I ran over and screamed and hit out at their hands. Tommy ran over too and joined in too, and we got him away!”

Don’t look for your Luckies in their familiar green package on the tobacco counters. No, your Luckies are wearing a different color now.

Who the hell knew what was going to happen? After Pearl Harbor, the world had turned upside down, and Frank had to grab whatever he could. And so he began to pester Tommy relentlessly, always mentioning the Billboard poll: C’mon, Tom. Lemme record a few on my own. We’ll sell some records. C’mon!

Jesus Christ, Frank, Dorsey finally said. All right. Just to shut you up.

Frank rehearsed constantly for the next three weeks, afternoons at the Palladium nightclub, in Los Angeles, before Tommy showed up, just Frank and Lyle (Skitch) Henderson or Joey Bushkin on the piano behind him, in the quiet stillness of the huge, empty dance hall. He knew exactly which songs he wanted to wax. They were all ballads, naturally, all dripping with romance: there was “The Night We Called It a Day,” by these new kids Matt Dennis and Tom Adair, who’d written “Let’s Get Away from It All” and “Violets for Your Furs.” There was a sweet Hoagy Carmichael number that hadn’t been recorded much, “The Lamplighter’s Serenade.” And then two classics: Kern and Hammerstein’s “The Song Is You” and Cole Porter’s equally immortal “Night and Day,” whose lyrics he’d once blown in front of the great man himself when Porter stopped by the Rustic Cabin.

Frank had told Dorsey that he wanted strings. Oh, how he wanted them. He loved the way they carried his voice, like a vase holding a bouquet of flowers, and he knew just the man to make them sing.

Axel Stordahl was a first-generation Norwegian-American from Staten Island who had joined the Dorsey band as fourth trumpeter in the mid-30s. He was a less than stellar horn player, but it quickly became clear that he had a gift for arranging ballads. When Sinatra joined the band, it was as if he and Axel had each found his missing piece. Physically and temperamentally, the two couldn’t have been more different: Stordahl, who was tall, bald, and pale-lashed, looked like nothing so much as a Norwegian fisherman. He even wore a fisherman’s cap and smoked a pipe. He was intensely calm, quietly humorous. Sinatra, who liked to nickname people he was fond of, called him Sibelius.

Frank Sinatra was the opposite of calm. Yet when he sang slow numbers, some sort of ethereal best self took over, and Stordahl’s writing helped him attain it. The pattern had been set on the singer’s first two recordings with Dorsey, “The Sky Fell Down” and “Too Romantic,” and it had continued on dozens of ballads he’d done (and Buddy Rich had grimaced through) with the band.

The recording session, which took place at RCA’s Los Angeles studios on the afternoon of Monday, January 19, 1942, went off perfectly. Pointedly, there was no drummer. Nor did Dorsey attend the session—both of the singles that resulted (released on RCA’s discount Bluebird label) were credited to Frank Sinatra with “Orchestra conducted by Axel Stordahl.”

Sinatra had been a wreck in the weeks leading up to the session. Whenever he wasn’t rehearsing, he was fretting about the huge implications of leaving Dorsey. No band singer had made it on his own since Crosby went solo, in 1931. (Though Dick Haymes, who’d replaced Sinatra in Harry James’s band, was trying some solo club dates in between engagements as Benny Goodman’s boy singer.) “[Frank] was almost tubercular,” Nick Sevano said. “He was seeing all kinds of doctors, but he was so nervous that he couldn’t eat. He never finished a meal… He started talking a lot about death and dying… ‘I get the feeling that I’m going to die soon,’ he’d say.”

Yet when he walked into the studio that Monday afternoon, it was with a swagger. Harry Meyerson, the Victor A&R man who ran the session, remembered, “Frank was not like a band vocalist at all. He came in self-assured, slugging… He stood his ground and displayed no humility, phony or real.”

In fact, it was the bravado that was phony—half phony, anyway. The fact of the matter was that Frank Sinatra was scared shit-less. But (true to a pattern he would maintain for the rest of his life) when he was afraid, he liked to make others jump.

A few days later, when the first pressings of the recordings came in, his fear diminished considerably: they were terrific. Axel Stordahl later recalled sitting for an entire sunny afternoon in Sinatra’s room at the Hollywood Plaza, listening to the four songs over and over on the singer’s portable record player. “He was so excited you almost believed he had never recorded before,” Stordahl said. “I think this was a turning point in his career.”

Between the lines, Sibelius sounds a little distanced from the exultation, perhaps a bit regretful at not having been able to get out and enjoy that glorious Los Angeles afternoon. That was the way it was, though, when you were close to the drama that was Sinatra: you stayed put in your orchestra seat until the performance was through.

Connie Haines remembered listening to Sinatra’s “Night and Day” with some of the rest of the band not long afterward: “Frank sat on a stool. He had on one of those hats Bing Crosby had made popular. It was slouched down over his head at just the right angle, and he had a pipe in his mouth… As the last note ended, we all knew it was a hit. The musicians rose to their feet as if one. They cheered. Then I heard him say, ‘Hey, Bing, old man. Move over. Here I come.’ ”

The story of Frank Sinatra’s life is one of continual shedding, both of artistic identities and of associates and intimates who had outlived their usefulness. The saga of his disentanglement from one of his most powerful relationships, his deep emotional and artistic bond with Tommy Dorsey, is complex and bewildering. Out of forgetfulness, self-protection, and self-mythification, Sinatra sowed no small amount of the confusion himself. When a man he admired, Sidney Zion, was bold enough to ask him, in front of an audience at Yale Law School, about the fabled role of organized crime in the tale, Sinatra parried with a genteel vagueness that befitted the surroundings—and that let himself almost completely off the hook.

“Now, in the story that is told in The Godfather, about how you happened to get let out of the contract of Mr. Dorsey, it is said that somebody came there and put a gun at his head or whatever,” Zion offered. “There’s been a million stories … and I think it would be interesting to set it straight.”

Sinatra, 70 and dignified now, smiled in a distinguished way and proceeded to set the record anything but straight. “Well, it’s quite simple, really,” he said. “The reason I wanted to leave the orchestra was because Crosby was number one, way up on top of the pile, and in the field were some awfully good singers with the orchestras. Bob Eberly with Jimmy Dorsey’s orchestra was a fabulous vocalist. Mr. Como was with Ted Weems, and he still is such a wonderful singer. I thought if I don’t make a move out of this band and try to do it on my own soon, one of those guys will do it, and I’ll have to fight all three of them, from Crosby all the way down to the other two, to get a position. So I took a shot and I gave Mr. Dorsey one year’s notice. It was in September whatever year. I said, ‘I’m going to leave the band one year from that day.’ Beyond that year, I had another six months to do in the contract. He said, ‘Sure.’ That’s all he said, was ‘Sure.’ ”

Sure.

In fact, Mr. Sinatra gave Mr. Dorsey his notice in February of 1942, with 10 months left to run on the three-year contract he’d signed in January 1940, and he would continue to sing with the Dorsey band for just 7 of those months, and it is quite unlikely that Tommy Dorsey responded to this highly unwelcome news with a simple “Sure.”

We have this last from no less an authority than Art Linkletter—yes, the Art Linkletter, who as a young radio host in February 1942 went backstage at San Francisco’s Golden Gate Theatre to interview Tommy Dorsey and found that Sinatra had just given notice, and that Dorsey was not happy. “He’s such a damn fool,” the bandleader vented to Linkletter. “He’s a great singer, but ya know, you can’t make it without a band… Does he think he can go out on his own as good as he is?… It upsets me because he’s an important part of our band.”

What Dorsey wouldn’t say—or couldn’t bring himself to say—was how betrayed he felt by Sinatra. This was a boy he had taught his deepest art, a boy he had elevated to national fame! A boy who had sat up till all hours playing cards with him, one who, despite the mere 10 years’ difference in their ages, had been like a son to him—and who had treated him, in many ways, like a father. And now, inevitably, the youth was leaving the nest. The bandleader was a tightly wound, thickly self-protected man, one who nursed his hurts deep in the sub-basement of his soul, and this was a wound that would stay with him till the end of his days.

Good Luck, Kiddo

Sinatra played out what was left of his tenure with Dorsey, excited about his next stop: Columbia Records had agreed to sign him as a solo singer, an almost unprecedented move for an unprecedented artist. But the furious bandleader wasn’t letting go easily. He would advance Frank $17,000 to start his solo career—but in exchange for his release, Dorsey told the singer, he had to sign a contract promising 33 1/3 percent of his future earnings to Dorsey. Sinatra smiled and signed. Ever his tough mother’s son, he didn’t intend to pay Tommy a quarter. How he got out of the contract is a convoluted saga, possibly entailing some of the elements alluded to in The Godfather—a friend and early sponsor of Frank’s was the New Jersey gangster Willie Moretti, who may or may not have made a threatening phone call to Dorsey—but also involving less sexy characters such as lawyers and talent agents, making sure that both their nests and Sinatra’s were feathered. In the end, Frank got out, and Dorsey got $60,000 ($750,000 in today’s dollars).

Sinatra made his last radio broadcast with the Dorsey band on September 3, 1942, at the Circle Theater, in Indianapolis. On the intro to “The Song Is You,” you can sense the chaos under Tommy’s steely-smooth, slickly cadenced patter: “After tonight,” the bandleader tells the Hoosier audience, “he’s going to be strictly on his own. And Frank, I want to tell you that everyone in the band wishes you the best of luck.”

“Thanks, Mac,” Sinatra says, using the nickname Jimmy Dorsey had given his brother when the two were boys. The singer’s voice sounds very young, very Hoboken, and—surprisingly—soft with emotion. “I’d like to say that I’m gonna miss all you guys after kickin’ around for three years. And ladies and gentlemen, I’d like you to meet the boy who’s gonna take my place as the vocalist with Tommy and the band. He’s a fine guy, a wunnerful singer, and he was good enough for Harry James and Benny Goodman, and—that’s really sayin’ plenty. Folks, I’d like you to meet Dick Haymes.”

After a nice round of applause, Haymes pipes up: “Well, Frank, I don’t know if anyone can really take your place with this band. But I’m gonna be in there tryin’. You can bet on that. As for you, well, I know that you’ll be knockin’ ’em dead on your own hook.”

Then it’s almost as if Dick Haymes actually gets the hook—Dorsey jumps right back in, just about cutting him off: “I agree with you there, Dick, and thanks a lot, Dick Haymes. Frank, before you hit the road, how ’bout one more song just for auld lang syne.”

“That’s all right with me, Tom,” Sinatra says. “Gimme the beat on our arrangement of ‘The Song Is You,’ and I’ll see what I can do with it.”

It’s all old-style showbiz, phony modesty an inch thick, but when Sinatra shifts from those Hoboken street tones to the first few bars of the Kern-Hammerstein masterpiece, you do a double take: the Voice is that rich, gorgeous, and expressive. Look out, world, here I come is the clear message—along with a quick Good luck, kiddo to Dick Haymes. And a quick thumb of the nose to Tommy Dorsey.

The way he ends the song—an ethereal falsetto high F—has an infinitely vulnerable sound: as always, his emotions were powerful and complicated. Dorsey told a magazine writer years later that at a party backstage after the final show Sinatra “was literally crying on my shoulder … depressed about what would happen to his career.” Depressed? Good and scared was more like it. He had Tommy’s 17 grand in his pocket, but that would burn fast, especially with the way he spent. What he didn’t have were bookings. His agent, Frank Cooper, had managed to land him a bit part singing one number, “Night and Day,” in a Columbia B picture, Reveille with Beverly, and his rabbi at Columbia Records, Manie Sacks, had wangled him a spot on a CBS radio show in New York. Period. Besides that, it was going to be strictly Sit and Wait.

He was terribly frightened. Excited too—he believed in his luck. But some part of him always felt like that kid in bed in the dark on Monroe Street in Hoboken, listening through the wall as his mother rattled on and on, and his old man just lay there, grunting.

As for the Sentimental Gentleman of Swing, Tommy Dorsey was drinking a good bit in Frank’s final days with the band, and liquor always put a fine edge on his cold Irish anger. Sinatra may have cried on his shoulder, but when all was said and done, Dorsey had seven words for him.